In an era when so few players manage to make 500 appearances for a single club, let alone as captain, Terry’s personal milestone confirms his legend at Chelsea and in the English game.
Terry has often divided opinion throughout his career, with his life off the pitch often leading to criticism of him on it.
Separate the two, though, and Chelsea have a player of considerable class who should be looked upon as being among the finest of his generation.
Terry has won it all in football. He has captained Chelsea to three Premier League titles, four FA Cups, two League Cups and was essential in his team’s path to glory in their 2012 Champions League success, followed up a year later with the Europa League.
His pace, or lack thereof, has often been cited as a major weakness, but such is Terry’s commanding presence and reading of the game, he has rarely left himself isolated where opponents have exploited him.
When we’re talking defenders, his ability cannot be questioned. When we’re talking captains, his reputation is only strengthened.
Chelsea’s history is one full of glamorous names and winners who have worn the armband, leading the club into battle.
In the very early days, there was the significant figure of Willie “Fatty” Foulke who was later followed by the likes of Roy Bentley, Ken Armstrong and Terry Venables—all stars of their era.
Then there was Ron Harris, a man still known as Chopper along the King’s Road despite his retirement more than 30 years ago.
“The saying has always been that when the going gets tough, the tough get tougher,” Harris said when speaking to Bleacher Report this week.
“John’s always been in the thick of things, putting himself about and leading from the front. What more can you say about the fella?”
Harris was the first captain to win the FA Cup with Chelsea when he led the club to victory over Leeds United in 1970.
A year later, Chelsea beat the might of Real Madrid to lift the European Cup Winners’ Cup with Chopper as captain.
He remains a respected figure to this day, and when he speaks, people often listen.
“I can’t speak highly enough of John and everything he has done for Chelsea Football Club,” he continued.
“It’s a proud moment for me to see him making his 500th appearance as captain. Like me, he has come through the ranks and gone on to captain the club to win major honours.
“The only thing I ever say to John is that he can’t beat my record of 795 appearances as a Chelsea player! I like to tell him that regularly!”
Whereas Harris has watched Terry’s career blossom from afar, watching him replicate his own success from the youth team at Stamford Bridge right through to the first XI, Marcel Desailly was there when it all started.
A World Cup winner with France in 1998, Desailly had a massive impact at Chelsea when he arrived that summer from AC Milan.
The Frenchman brought with him a culture that had been missing—something Terry was wise enough to absorb while playing the role of Desailly’s understudy.
Even back then, though, Desailly—who also went to captain the Blues—says he saw something special about his former teammate.
“I had the privilege of seeing him arriving on the scene as a very young player. He was very motivated and was already ready to become an elite player,” Desailly told us.
“Every day he was first at training. He would talk to the older players. He was young, but he was a leader. He was already a captain.”
Jose Mourinho didn’t take long to notice those leadership qualities, and when appointed manager in 2004, he made Terry his captain.
It says a lot that Mourinho built his new team around Terry.
With the financial clout of Roman Abramovich behind him, Mourinho could have turned to a more experienced name, but he chose Terry.
And he never let him down.
Indeed, Terry has never let Chelsea down. There have been moments when his behaviour has put an unwanted spotlight on the club, but throughout his 10 years as captain, his influence has been significant.
He’s everything the club could have wanted, and in an era where players come and go, moving from club to club, he has helped Chelsea ensure a culture has remained in the dressing room.
“He’s been a great captain for the times,” Harris added.
“He’s held everything together at Chelsea in the modern era when there have been so many changes. He’s been a player the fans could relate to, the one they all look up to.”
Harris' view is echoed from the terraces.
"John Terry's strength, courage, passion and willingness to fight for every ball as well as the fact that, if you cut him, he’d bleed blue, are some of the reasons that he’s loved by the Stamford Bridge supporters," explained David Johnstone, a well-known Chelsea fan and also editor of the respected fanzine cfcuk.
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"Those who castigate him don’t know him," Johnstone added. "Terry's undoubtedly one of the best defenders of his generation."
It’s for reasons such as those that many will point to him as being Chelsea’s greatest player to have donned the armband.
He’s led the club through its greatest period, and on silverware alone, it’s difficult to argue otherwise.
But then the likes of Dennis Wise, Colin Pates, Ray Wilkins and Chopper himself enjoyed different forms of success that were equally vital to Chelsea’s history.
It’s been a monumental journey for Terry, one to be marvelled at and celebrated, although Harris stopped short of labelling him the finest.
“I’d say the greatest captain is Ron Harris!” he quipped.
A mark of Terry’s character will come at the final whistle against Palace on Saturday.
It may well be his 500th game as captain, but without three points on the board, it will mean little to him.
And that’s the mark of John Terry: captain, leader, legend.
*All quotes taken firsthand unless otherwise noted.
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Garry Hayes is Bleacher Report's lead Chelsea correspondent. Follow him on Twitter @garryhayes.